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C5157

Campesterol

Name: Campesterol
Brand: SIGMA

~65%

Sinónimos:

24α-Methyl-5-cholesten-3β-ol, 24(R)-Ergost-5-en-3β-ol

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Fórmula empírica (notación de Hill):

C₂₈H₄₈O

Número CAS:

474-62-4

Peso molecular:

400.68

UNSPSC Code:

12352211

NACRES:

NA.28

PubChem Substance ID:

24892762

EC Number:

207-484-4

Beilstein/REAXYS Number:

3216975

MDL number:

MFCD00010475

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Propiedades

biological source

Glycine max (soybean)

Quality Segment

200

form

powder

concentration

~65%

shipped in

ambient

storage temp.

−20°C

SMILES string

[H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])[C@H](C)CC[C@H](C)C(C)C

InChI

1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1

InChI key

SGNBVLSWZMBQTH-ZRUUVFCLSA-N

Descripción

Application

Campesterol was used as standard in GC and HPLC analysis of oil samples from plants.

Biochem/physiol Actions

Campesterol is a phytosterol, primarily found in nuts, fruits, legumes and seeds. Though an analogue of cholesterol, it is poorly absorbed in humans and competitively inhibits the absorption of cholesterol. Campesterol decreases the transcription of genes involved in cholesterol metabolism in hepatocytes and enterocytes and has positive impact in treatment of cardiovascular disease.

Plant sterol. May lower absorption of dietary cholesterol.

Preparation Note

Campesterol yields clear, colorless to faint yellow solution in chloroform at 20 mg/ml.

Analysis Note

Appears ~98% by HPLC and GC, but has been shown by ¹³C-NMR to contain ~35% dihydrobrassicasterol (24β-methyl-5-cholesten-3β-ol; 24[S]-ergost-5-en-3β-ol).